GB944838A - Improvements in or relating to colour couplers and to their production and use in colour photography - Google Patents

Improvements in or relating to colour couplers and to their production and use in colour photography

Info

Publication number
GB944838A
GB944838A GB43668/59A GB4366859A GB944838A GB 944838 A GB944838 A GB 944838A GB 43668/59 A GB43668/59 A GB 43668/59A GB 4366859 A GB4366859 A GB 4366859A GB 944838 A GB944838 A GB 944838A
Authority
GB
United Kingdom
Prior art keywords
acid
reacted
compound
chloride
colour
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB43668/59A
Inventor
Colin William Greenhalgh
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ilford Imaging UK Ltd
Original Assignee
Ilford Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL259369D priority Critical patent/NL259369A/xx
Application filed by Ilford Ltd filed Critical Ilford Ltd
Priority to GB43668/59A priority patent/GB944838A/en
Priority to US75081A priority patent/US3161512A/en
Priority to DE19601445078 priority patent/DE1445078A1/en
Priority to FR847887A priority patent/FR1276582A/en
Publication of GB944838A publication Critical patent/GB944838A/en
Priority to US336369A priority patent/US3236861A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36Oxygen or sulfur atoms
    • C07D207/402,5-Pyrrolidine-diones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36Oxygen or sulfur atoms
    • C07D207/402,5-Pyrrolidine-diones
    • C07D207/4162,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32Colour coupling substances
    • G03C7/3212Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07Organic amine, amide, or n-base containing

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Indole Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0944838/C2/1> wherein A is a trivalent radical derived from 1,2-phenylene, 2,3-naphthylene or di- or trimethylene, B is a colour coupler residue, Y is -CO-, -CONH-, -COCH2- or -COCH2S- and R is a hydrocarbon group which may be substituted. The residue B is such that BNH2 will react with the oxidation products of N,N-diethyl-p-phenylenediamine, formed during the development of a silver salt image with that compound, to yield a quinoneimine or azamethine dyestuff. Such compounds are prepared by reacting with BNH2 a compound of formula Z-A(CO)2N-R wherein Z is -COX, -CH2COX, -NCO, -NHCOOC6H5 or -SCH2COX and X is halogen. In examples, R is a 4, 6, 8, 10, 12, 14, 16 or 18C alkyl group, or 4-dodecylphenyl, benzyl or cyclohexyl and B is 5-keto-1-phenylpyrazol-3-yl, 4 - (4 - methoxybenzoylacetamido) - 3 - methoxyphenyl, b -(1-hydroxy-2-naphthamido) ethyl, 4-cyanoacetylphenyl or 4-(3, 5-dimethoxycarbonylphenyl) carbamylacetylphenyl. Starting materials. (1) Trimellitic anhydride reacted with octadecylamine to give 4-carboxy-N-octadecylphthalimide which gave the 4-chlorocarbonyl compound with thionyl chloride. Other N-alkyl-4-chlorocarbonyl-phthalimides were similarly obtained. (2) Octadecylamine reacted with 4-nitrophthalic anhydride to give 4-nitro-N-octadecylphthalimide which was reduced with Raney Ni to the 4-amino compound; reaction of the latter with phosgene gave 4-isocyanato-N-octadecylphthalimide. (3) Tricarballylic anhydride (from the acid and acetyl chloride) reacted with 4-dodecylaniline giving N(4-dodecylphenyl) succinimidoacetic acid from which the acid chloride was obtained using thionyl chloride; N-octadecylsuccinimidoacetic acid was similarly obtained. (4) Carboxymethylmercaptosuccinic acid reacted with 4-dodecylaniline giving N(4-dodecylphenyl) succinimidomercaptoacetic acid which afforded the acid chloride with thionyl chloride. The compounds are used as colour couplers (see Division G2) either directly or in dilute alkali, in which case the imide ring is opened. Specific alkaline hydrolysis products isolated-(Examples 26 and 27) are 41-methoxybenzoylacet-2-methoxy-5 (3- or 4-cyclohexylaminocarbonyl-4-or 3-carboxybenzoylamino) anilide and its analogue in which benzyl replaces cyclohexyl.
GB43668/59A 1959-12-23 1959-12-23 Improvements in or relating to colour couplers and to their production and use in colour photography Expired GB944838A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL259369D NL259369A (en) 1959-12-23
GB43668/59A GB944838A (en) 1959-12-23 1959-12-23 Improvements in or relating to colour couplers and to their production and use in colour photography
US75081A US3161512A (en) 1959-12-23 1960-12-12 Colour couplers and their production and use in colour photography
DE19601445078 DE1445078A1 (en) 1959-12-23 1960-12-23 Process for the preparation of color coupler compounds for color photography
FR847887A FR1276582A (en) 1959-12-23 1960-12-23 Improvements in color photography
US336369A US3236861A (en) 1959-12-23 1964-01-08 Organic imido compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB43668/59A GB944838A (en) 1959-12-23 1959-12-23 Improvements in or relating to colour couplers and to their production and use in colour photography

Publications (1)

Publication Number Publication Date
GB944838A true GB944838A (en) 1963-12-18

Family

ID=10429779

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43668/59A Expired GB944838A (en) 1959-12-23 1959-12-23 Improvements in or relating to colour couplers and to their production and use in colour photography

Country Status (4)

Country Link
US (2) US3161512A (en)
DE (1) DE1445078A1 (en)
GB (1) GB944838A (en)
NL (1) NL259369A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0782044A1 (en) * 1995-12-27 1997-07-02 Konica Corporation Silver halide light-sensitive color photographic material

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL268720A (en) * 1960-08-29
CH442985A (en) * 1963-10-08 1967-08-31 Gevaert Photo Prod Nv Method for obtaining color photographic images
NL133250C (en) * 1964-02-20
DE2447175A1 (en) * 1974-10-03 1976-04-15 Agfa Gevaert Ag LIGHT SENSITIVE MATERIAL WITH EMULSIFIED SUBSTANCES
JP5934658B2 (en) * 2013-01-29 2016-06-15 Jxエネルギー株式会社 IMIDE-UREA COMPOUND AND PROCESS FOR PRODUCING THE SAME, GREASE THINNER, AND GREASE COMPOSITION

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE435374A (en) * 1938-07-14
US2313498A (en) * 1940-01-02 1943-03-09 Eastman Kodak Co Cyanoacetyl coupler
US2452315A (en) * 1945-04-09 1948-10-26 American Maize Prod Co Plasticized prolamine-base protein compositions
US2628964A (en) * 1951-04-07 1953-02-17 American Cyanamid Co Preparation of naphthostyrils
US2663714A (en) * 1951-09-24 1953-12-22 Lilly Co Eli Hydrogenated benz [cd] indoles
BE516025A (en) * 1951-12-05
BE541727A (en) * 1954-10-01
US2857395A (en) * 1955-04-09 1958-10-21 Arnold Herbert Derivatives of alpha-n-(beta-dialkylamino alkyl)-amino-phenyl acetic acid esters
BE552264A (en) * 1955-11-01
BE565656A (en) * 1957-03-15
US2920961A (en) * 1957-07-29 1960-01-12 Eastman Kodak Co Couplers for color photography
US2897206A (en) * 1958-06-24 1959-07-28 Nippon Shinyaku Co Ltd Dialkylamides of alpha-(4-antipyrylamino)-fatty acids and their n-alkyl derivatives
BE590403A (en) * 1959-04-30

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0782044A1 (en) * 1995-12-27 1997-07-02 Konica Corporation Silver halide light-sensitive color photographic material
US5981157A (en) * 1995-12-27 1999-11-09 Konica Corporation Silver halide light-sensitive color photographic material

Also Published As

Publication number Publication date
DE1445078A1 (en) 1968-10-24
US3161512A (en) 1964-12-15
US3236861A (en) 1966-02-22
NL259369A (en)

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